


The Best Thirty Dollars Ever Spent

by renaissancejinx



Category: Batman - All Media Types, Batman: Under the Red Hood (2010), DCU, DCU (Comics), Red Robin (Comics)
Genre: Batfamily (DCU), Boys in Skirts, Crossdressing, Fluff and Smut, Gay, Humorous Ending, Jaytim - Freeform, Light Smut, M/M, Maid Costume, Sort of? - Freeform, batfamily groupchat, too smutty to be fluff and too fluffy to be smut
Language: English
Status: Completed
Published: 2021-01-13
Updated: 2021-01-13
Packaged: 2021-03-17 16:14:07
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,963
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28727916
Author URL: https://archiveofourown.org/users/renaissancejinx/pseuds/renaissancejinx
Summary: Tim Drake has a love for Tiktok that is normal for any guy his age. Usually, he doesn't partake in any of the trends on it. However, after the "boys in maid costumes" trend takes off, he realizes that he needs to convince Jason to try it. Just once. For science.
Relationships: Tim Drake & Jason Todd, Tim Drake/Jason Todd
Comments: 7
Kudos: 103





	The Best Thirty Dollars Ever Spent

**Author's Note:**

  * Translation into 中文-普通话 國語 available: [【授權翻譯】The Best Thirty Dollars Ever Spent](https://archiveofourown.org/works/29105631) by [rubylee2017](https://archiveofourown.org/users/rubylee2017/pseuds/rubylee2017)



> I thought of this idea while I was driving to work the other day, and I came home and wrote it one straight sitting. I needed to see this one written. Hope you enjoy!

“Absolutely not.” growled Jason definitively. Tim sighed loudly and rolled sideways in their bed, placing his head on Jason’s thighs.

“Why notttt?” whined Tim shrugging his shoulders. He kicked his feet lightly as he laid long ways across the bed, twirling the comforter between his feet. 

“Because it is stupid and humiliating and I won’t do it.” barked Jason still looking at his phone and not at Tim.

“Please?” asked Tim, trying to soften his voice. 

“Over my undead body.”

“But you’d look so good, all the guys on tiktok look so hot in them!”

“I don’-” started Jason, suddenly breaking away from his phone to look down at the younger man in his lap as if he had suddenly started listening to him. “Wait why are you looking at other guys on your phone?” asked Jason. He could be a bit possessive at times, but never in a way that upset Tim. Tim realized that it was supposed to be in a caring way and knew that if he told Jason he was being too possessive, he’d back off. Sometimes it felt nice to have someone who so fiercely claimed you as theirs. Especially when that someone was as attractive as Jason was.

“They just come up on my for you page, you know I only have eyes for you,” said Tim, tilting his mouth into a small, relaxing smile to let Jason know he had nothing to worry about. 

“I don’t know what most of those words meant.” said Jason, his voice monotone but for humorous intent. Tim had tried to convince him to get a tiktok for months at this point, mostly because he was tired of trying to explain tiktok trends to him but he had not been very successful on that front. Jason didn’t really understand the whole tiktok thing, he did however enjoy the ones Tim usually sent him. 

“Basically I can’t control if I see them or not. But that’s not important, what is important is,” Tim paused and took a deep breath in, as if preparing for a loud scream. “PLEASEEE! I’ll do anything you want Jay!” whined Tim, squirming in Jason’s lap. 

“Tim, let me make this clear. You could offer to blow me every day, twice a day, for the next year of my life, and I still wouldn’t do it.” 

“What about the next two years?” bargained Tim, half joking.

“No.” 

“Fine, fine, I didn’t want to do this, I wanted to try and keep this civil, but you’ve forced my hand.” said Tim, his voice impish and breathy. He then sat up, untwisted the blanket from his feet and climbed on top of Jason’s hips. He placed one knee down on either side of him, dropped his shoulders and pouted his bottom lip. He was wearing nothing except one of Jason’s sweaters, which was exceptionally large on him with the sleeves pooling just before the end of his finger tips, and a pair of boxer briefs. He could feel the fabric of Jason’s pajama bottoms against the back of his upper thigh. “Pretty please Jason, for me?” asked Tim in a cutesy voice, batting his eyelashes.

“No, this isn’t working Tim,” said Jason, whose head was turned away from Tim looking at the other side of the room. Not many people could convince Jason to do something he didn’t want to do, but Tim? He was the only person in the universe that if he said jump, Jason would consider asking how high. Especially when Tim was wearing his clothes. He really liked when Tim wore his clothes. 

“Are you sure? Then why won’t you look at me? Can’t you at least do that for me? Look at me?” asked Tim, leaning forward and placing a long, slender finger on Jason’s jawline. Jason cut a quick eye at him and then looked away. However, Tim made it very clear that this was not enough for him and dragged his finger from Jason’s jaw to his chin and slowly tried to turn the man’s head. Jason resisted for a second, but then allowed his head to be turned by Tim. 

“There. Happy now? I’m looking.” said Jason shortly. Jason had barely finished his response when Tim threw his arms around him and nuzzled his head into Jason’s neck. 

“I’m always happy when you’re around.” said Tim into the hollow of Jason’s collar bone. The words were hot and soft against his skin and sent chills up Jason’s spine. Jason felt the breath of the other man on his skin and his shoulders relaxed. He reached his hand up and played with Tim’s hair, running his fingers through it, playing with the ends of the longer pieces. Jason leaned forward and kissed the top of Tim’s head, smiling into his hair, smelling the linger scent of his coconut shampoo. Tim smiled into Jason’s skin, he knew he had got him. He peeked his head out from Jason’s shoulder, only revealing one eye and the corner of his mouth. “Please, Jay? It would make me so happy. ” 

Jason was lost in the soft scent of Tim, distracted by the feeling of silky locks in his fingertips. He didn’t want to say yes. He didn’t want to. Every logical part of his body tried to stop him, but he couldn’t hear them over the firing of his synapses as Tim’s scent lingered in his nose. Finally, he broke. 

“FINE.” said Jason exasperated and cranky that Tim was so good at convincing him to do what he wanted. Tim pulled away from Jason’s body and looked at him with a huge smile on his face. “I’ll do it. Just order the damn thing on Amazon I’ll do it already.” said Jason pretending to be grumpy, but missing the scent of Tim’s hair. When he said this, Tim’s smile dropped, and his mouth twisted to the side in humorous guilt. 

“Well about that…” started Tim deviously. He then rolled over Jason’s thighs and got off the bed, walked over to the closet and pulled out a small white Amazon box from the floor. “I kind of already did!” said Tim smiling a cheesily large smile holding up the box. Tim then placed the already opened box on the bed and pulled out a short black maid costume, with a small white apron on it. 

“I shouldn’t even be surprised.” said Jason deadpan. Jason then turned to get off the bed then stopped and looked at Tim with narrow eyes. “If I do this, there is to be no evidence of it. Or I will not be the only dead man in this apartment. Capisce?” 

“Deal! Yay! Thank you, thank you, thank you, thank you, thank you, thank you!” exclaimed Tim running over to Jason and throwing his arms around him. 

~~~

“It’s really…” started Jason, speaking from behind the bathroom door. “Short.” he continued, trying to pull down the end of the dress a little more, it barely reaching his upper thighs. Tim knew it would be, he may or may not have purposefully ordered it in a size too small for Jason. Just in case he couldn’t convince him to wear it, he could still wear it himself. Or just in case he did convince him to wear it. 

Tim fiddled with his phone, trying to set it up in the closet across from in a way that Jason wouldn’t see. He didn’t have any plans to share the picture he planned to take, but he did want one for himself as he wasn’t sure if he’d be able to convince him to wear it again. Plus, being able to have a picture of his boyfriend in a maid costume might be nice for away missions. You know, the ones with private rooms anyways. 

“It’s supposed to be! It’s a ‘sexy maid costume’ not a ‘conservative house keeper’ costume! Now come out and let me see!” called Tim, keeping his attention on the phone. Once he finally got it set up he made sure to press record, planning to just take a screenshot from the video later. 

“Uh… is the headband really necessary?” asked Jason, jingling one of the bells on the end of the cat ear headband. 

“Especially necessary! Now come on!” said Tim positioning himself so that he didn’t block the camera.

“God you are so impatient,” said Jason finally opening the door. Jason stood in the doorway and looked at his boyfriend. Tim stood with his mouth agape, the upper corners of his mouth creeping up, an audible breath meandering out of his mouth like it was made of tar. The maid costume was, flattering, on Jason to say the least. The cheap black fabric was taut against his chest, his pecks pushing the edges of the fabric. It was also practically bursting at his arms. The skirt was a lot shorter than Tim imagined it would be, even at the smaller size sitting just barely on Jason’s thigh, and even then his defined thigh muscles stretched the fabric. Tim’s eyes rested for a second in between Jason’s legs, where the fabric was stretched tighter than anywhere else, highlighting the impressive length of his boyfriend. He felt his stomach quiver when he looked at it. For a brief second he wondered what he was wearing underneath, until he felt resistance from the spandex of his underwear and remembered it was his turn to say something. 

“Wow. You look, wow.” choked out Tim finally after a few minutes. He could feel his face starting to warm up. Jason scratched at the back of his neck and looked away from Tim, the costume feeling like it was going to rip when he lifted his arm. He quickly put his arms back down when he felt the bottom of the skirt rise up, the brief flash of skin that showed answering Tim’s earlier thought about what he was wearing underneath. 

“Thank you. Now can I take this stupid thing off?” asked Jason, embarrassed about flashing his boyfriend, which he knew was stupid but couldn’t help. 

“Wait not yet! You just put it on! You look…” Tim finally felt his face turn bright red. “Sexy,” said Tim unable to look Jason in the eye. “Don’t take it off yet.” pleaded Tim his voice trailing off at the end. Jason smiled slyly. 

“Sexy?” asked Jason, his voice coy. “Tim Drake is this turning you on?” asked Jason, the tone of his voice mocking chastisement. Tim felt his face grow hotter. Jason began to slowly walk towards him, the movement of the maid costume as he walked only further fogging Tim’s brain. 

“Um, it’s um-” Tim scratched at the back of his neck trying to remember any words he knew. He felt his 750 on the english section of the SAT scowling at his inability to remember any of the words. 

“Because if it is, I could help.” said Jason, approaching the young man. He leaned close into Tim’s ear and placed a finger inside the leg hole of Tim’s underwear. “It is a maid’s duty to serve after all.” whispered Jason, the hot breath against Tim’s ear ran tingles down his spine and he felt the resistance in his underwear grow stronger. 

“You um- You are pretty dedicated to your um- duty.” said Tim, trying to match the sexiness of Jason, but still being distracted by the feeling of Jason’s finger on his skin. Jason was always better at being sexier than him. Tim blamed the age gap. Jason smirked, took his finger out of Jason’s leg hole, then grabbed the waistband, and jerked Tim closer. Tim could feel Jason’s dick against his thigh through the maid costume, his breath hitched.  
“Go sit on the bed, you’ll see just how dedicated.” 

~~~

Tim had already thought this when he first saw Jason in the maid costume, however after the night they had? He decided then and there, that was the best 30 dollars he had ever spent. Ever. 

After they had finished Tim fought off the sleepiness that batted against his eyelids. He waited until he was sure that Jason was sleeping and creeped over to the closet. Quietly he opened it and pulled his phone out of the position he had propped it up in. He then stopped the video that was recording, made sure his volume was all the way down as there was definitely some… loud noises in it, and began to scrub through the beginning. Once he found a good clear shot of Jason he screen shotted it and made sure to delete the rest of the video. Just to be safe. 

Tim looked at the photo of Jason on his screen, smiling at the beautiful man, in awe of the fact that a man like Jason chose someone like himself. Tim couldn’t lie, it was definitely a self esteem booster, to have such an attractive man want to be with him. A small part of him wanted to brag to the whole world about how beautiful Jason was and how lucky Tim was to have him. Suddenly he had an idea, and he knew it was a bad one.

He looked at the clock in the corner of his phone, 3:34 AM, and then back at the picture. The idea lurked in the back of his mind, daring him to do it. Tim knew he couldn’t tell the whole world, mostly because he liked his life, but he knew he wanted to show someone. This was a once in a lifetime opportunity, he couldn’t be the only one who saw it. 

Quickly, he jumped to the message app in his phone and began to sift through his texts. He looked over at where the contact images were supposed to be, however only grey letters appeared as he was really bad at putting in contact photos for people, and began sifting through the text messages. He didn’t look at the names of the people, just the letters, mostly because he knew who he regularly texted and partly because he was exhausted and didn’t feel like reading out individual names. He knew he couldn’t send it to Bart, he couldn’t keep a secret for his life. He thought about Cassie, but then decided that maybe sending your ex-girlfriend kinda scandalous pictures of your current boyfriend might not be a good idea, no matter how close you guys were. 

Finally, he settled on Steph, believing that she could keep a secret and that she would also appreciate the fact that he got Jason to wear it. Tim scrolled in his messages, found the large gray S and sent it the photo without a caption or looking at any of the other texts. Once doing this he walked over to his bed and collapsed into it, wiggling his way into Jason’s arms and falling asleep.  
~~~

Tim woke up before Jason the next day, something he would be quickly grateful for. After wiping the eye crust from his bed he reached for his phone that was sitting on the nightstand. On his screen the numbers 11:45 were brightly displayed, underneath a series of texts from the bat-family group chat that Dick had named “Orphans with Daddy Issues” and wouldn’t let anyone change. 

Tim opened his phone and clicked on the message app. He then noticed the giant, familiar, gray S next to the group chat and felt his stomach drop. For the first time, he also noticed the other, smaller letters next to it that he didn’t recognize the night before. Anxiously, he clicked on it, scrolled back up to the top of the chat, and saw the photo of Jason in the maid costume, which looked even shorter at 12 PM than it did at 12 AM. 

He rationalized that in his tired haze last night, he had confused the group chat for his and Steph’s texts, due to both of them having the gray letter S. He considered briefly leaving the apartment, faking his death, and becoming a sheep farmer in middle Europe, but decided that Jason would still be able to find him there. He was so dead. Nervously, he scrolled through the texts from his friends. 

Dick-face: OMG. NICE LEGS JASON.

Steph: Yeah all three of them, christ Tim are you okay

Dick-face: I GUESS WE KNOW WHY THEY CALL YOU THE RED HOOD NOW. YIKES 

BG: Well. I’ll never unsee that.

Duke: It’s definitely uh memorable

Cass: ...

Satan Spawn: Really Todd? I’d expect this from Drake, but you? How could you be so foolish.

Horrified, Tim put down his phone on the nightstand and buried his head into his hands. He had never been so humiliated, and was just grateful that he didn’t send it to the one with Bruce in it as well. 

He then spent the rest of his afternoon waiting for Jason to wake up, fruitlessly trying to do small tasks around the apartment, or trying to work on a case but would ultimately find himself distracted, waiting for the eventual moment when he would get choked from behind, or unexpectedly shot in the head by Jason. Finally he heard the yell come from his bedroom. 

“Timothy Jackson Drake!” The middle name. He was in trouble. Big trouble. Maybe being the second dead Robin wouldn’t be so bad he thought, it’s only two letters away from Red Robin. Tim turned towards his bedroom where Jason stood, with unadulterated rage in his eyes, which Tim thought was his regular look for a long time, but turns out, this was worse. 

Tim didn’t know what was going to come next, besides the fact that one, it was going to hurt, and two, it was still the best thirty dollars he ever spent.

**Author's Note:**

> Thanks for reading! Hope you enjoyed it and found the ending some what humorous!


End file.
